EP1700877A1 - Poly(uréthanecarbonate) polyols - Google Patents

Poly(uréthanecarbonate) polyols Download PDF

Info

Publication number
EP1700877A1
EP1700877A1 EP06003902A EP06003902A EP1700877A1 EP 1700877 A1 EP1700877 A1 EP 1700877A1 EP 06003902 A EP06003902 A EP 06003902A EP 06003902 A EP06003902 A EP 06003902A EP 1700877 A1 EP1700877 A1 EP 1700877A1
Authority
EP
European Patent Office
Prior art keywords
poly
polyols
carbonate
urethane
phenol
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP06003902A
Other languages
German (de)
English (en)
Inventor
Hartmut Dr. Nefzger
Manfred Dr. Schmidt
James-Michael Barnes
Erika Bauer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Covestro Deutschland AG
Original Assignee
Bayer MaterialScience AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer MaterialScience AG filed Critical Bayer MaterialScience AG
Publication of EP1700877A1 publication Critical patent/EP1700877A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/44—Polycarbonates
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
    • F16B—DEVICES FOR FASTENING OR SECURING CONSTRUCTIONAL ELEMENTS OR MACHINE PARTS TOGETHER, e.g. NAILS, BOLTS, CIRCLIPS, CLAMPS, CLIPS OR WEDGES; JOINTS OR JOINTING
    • F16B43/00—Washers or equivalent devices; Other devices for supporting bolt-heads or nuts
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/46—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen
    • C08G18/4615—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
    • C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
    • C08G18/8009—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203
    • C08G18/8012—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203 with diols
    • C08G18/8016—Masked aliphatic or cycloaliphatic polyisocyanates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/02—Aliphatic polycarbonates
    • C08G64/0208—Aliphatic polycarbonates saturated
    • C08G64/0225—Aliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen
    • C08G64/0241—Aliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen containing nitrogen

Definitions

  • the present invention relates to poly (urethane carbonate) polyols, a process for their preparation and their use.
  • Homopolymers or copolymers, hydroxy-functional, aliphatic polycarbonates are known. They are used in the field of high-quality polyurethane materials with high hydrolysis resistance. They are usually prepared from non-vicinal diols by reaction with diaryl carbonate ( DE-A 19 15 908 ) or dialkyl carbonate ( DE A 25 55 805 ). Furthermore, aliphatic polycarbonate diols from non-vicinal diols by reaction with Dioxolanonen ( DE-OS 25 23 352 ), Phosgene ( DE-OS 15 95 446 ), Bischloroformates ( DE-OS 8 57 948 ) or Urea (Angew. Chem. 92 (1980) 742 ) getting produced.
  • Dioxolanonen DE-OS 25 23 352
  • Phosgene DE-OS 15 95 446
  • Bischloroformates DE-OS 8 57 948
  • Urea Angew. Chem. 92 (1980) 7
  • adipic acid-based oligoesters DE-OS 19 64 998
  • Oligoesters based on caprolactone DE-OS 17 70 245
  • low molecular weight adipates EP-A 364 052
  • oligomeric tetraethylene glycols DE-OS 22 21 751
  • tetrabutylene glycols A disadvantage of these building blocks is their easily hydrolyzable ester group or the increased hydrophilicity, which leads at least to a greater swelling of the PUR molded body produced therefrom. Ether phenomenon containing polyether carbonates in turn have a reduced weather resistance.
  • polycarbonate polyols based on so-called dimer diols have been described ( US-A 5,621,065 ), which also result in a mixture with, for example, 1,6-hexanediol polycarbonates with reduced melting point and reduced viscosity.
  • dimer diols C36 mixtures
  • shorter-chain diol-based copolycarbonate polyols are also liquid at room temperature, they are usually comparatively highly viscous.
  • polyurethane carbonates which are prepared by reacting polycarbonates with low molecular weight diamines ( EP-A 624 614 ).
  • Polyols also contain free amino end groups.
  • amino alcohols DE-A 196 19 237
  • Polyurethane carbonates are obtained with hydroxyl end groups.
  • both of the latter methods of preparing polyurethane-carbonate polyols have the disadvantage of being a molecular weight-degrading reaction, i. the higher the proportion of the diamine, or of the amino alcohol, the higher molecular weight and thus more complicated to prepare, the polycarbonate used as the starting compound must be selected.
  • a further disadvantage is that only half of the functional groups, namely the amino groups, participate in the reaction in amino alcohols.
  • poly (urethane carbonate) polyols can be obtained by pre-reacting low molecular weight polyols with polyisocyanate to form a prepolymer having terminal OH groups and then polycondensing with carbonic acid derivatives.
  • the invention therefore provides poly (urethane carbonate) polyols and a process for their preparation.
  • the poly (urethane carbonate) polyols according to the invention have terminal hydroxyl groups and contain structural units of the general formulas ⁇ O- [R 1 -OC (O) -NH-R 2 -NH-C (O) -O-] a R 1 -O ⁇ n and [-C (O) -O] wherein R 1 is the same or different alkylene, cycloalkylene, or oxaalkylene groups having 4 to 12 C atoms, R 2 is alkylene or cycloalkylene groups having 6 to 14 C atoms, and a and n refer to the individual species natural numbers, based on the molecular ensemble also broken numbers.
  • Preferred radicals R 1 are 1,4-butylene, 1,5-pentylene, 1,6-hexylene, 3-methyl-1,5-pentylene, 1,7-heptylene, 1,8-octylene, 1,9-nonylene , 1,10-decylene, 1,12-dodecylene, 3-oxa-1,5-pentylene, 3,6-dioxa-1,8-octylene, 3,6,9-trioxa-1,11-undecylene and 7 oxa-1,13-tridecylene.
  • Preferred radicals R 2 are 1,6-hexylene, 1,8-octylene, isophorylene and 4,4'-dicyclohexylmethylene.
  • the poly (urethane carbonate) polyols according to the invention can be prepared by reacting aliphatic polyols and aliphatic polyisocyanates to prepolymers having terminal hydroxyl groups and then polycondensing these prepolymers with carbonic acid derivatives.
  • the OH-terminated prepolymers are preferably prepared by reacting low molecular weight polyols HO-R 1 -OH with polyisocyanates OCN-R 2 -NCO.
  • suitable low molecular weight polyols are 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 3-methylpentane-1,5-diol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol , 1,10-decanediol, 1,12-dodecanediol, oligomers of 1,6-hexanediol, of ethylene and propylene glycol, for example diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol or tetrapropylene glycol.
  • trimethylolethane trimethylolpropane or pentaerythritol
  • dimer diols eg Pripol® 2033 from Uniqema
  • hydroxyl-functional derivatives which can be prepared by esterification from the low molecular weight polyols. Suitable reaction components for such esterified derivatives are, for example, the dicarboic acids succinic acid, glutaric acid and adipic acid, as well as phthalic acid and compounds derived from ⁇ -caprolactone.
  • mixtures of representatives of the group of low molecular weight polyols and their esterified derivatives can be used.
  • Polyisocyanates suitable for preparing the OH-terminated prepolymers are aliphatic or cycloaliphatic, predominantly difunctional, isocyanates. Examples include: 1,6-hexamethylene diisocyanate, 1,8-octamethylene diisocyanate, isophorone diisocyanate, cis, trans-4,4'-methylene-bis (cyclohexyl isocyanate), trans, trans-4,4'-methylene-bis (cyclohexyl isocyanate), and NCO prepolymers made using these polyisocyanates. Of course, mixtures of representatives of this group can be used.
  • the preparation of the OH-terminated prepolymer according to the invention is carried out at temperatures above 23 ° C, preferably above 50 ° C, more preferably from 60 to 135 ° C, wherein the presence of a catalyst is not absolutely necessary. Normally, the reaction is carried out under nitrogen at normal pressure, but it can also be carried out under reduced or elevated pressure.
  • the molar mixing ratio of polyol and polyisocyanate component is measured by the desired ratio of urethane to carbonate groups in the later end product.
  • the resulting OH-terminated prepolymer is then further reacted with a carbonic acid derivative R 3 -C (O) -R 4 from the group of diaryl, dialkyl carbonates or ⁇ , ⁇ -bischloroformates.
  • a carbonic acid derivative R 3 -C (O) -R 4 from the group of diaryl, dialkyl carbonates or ⁇ , ⁇ -bischloroformates.
  • suitable diaryl carbonates are diphenyl carbonate and ditolyl carbonate
  • suitable dialkyl carbonates are, for example, dimethyl carbonate and diethyl carbonate. Particularly preferred are diphenyl carbonate and dimethyl carbonate.
  • Preferred ⁇ , ⁇ -bischloroformates are those which can be prepared from low molecular weight polyols, particularly preferably 1,4-butanediol bischloroformate and 1,6-hexanediol bischloroformate, and also the ⁇ , ⁇ -bischloroformate of bisphenol A. Further preferred is phosgene.
  • the OH-terminated prepolymers are reacted with the carbonic acid derivative R 3 -C (O) -R 4 , the temperature being 120 ° to 220 ° C., preferably 120 ° C. to 200 ° C., and a pressure of 0.1 to 200 mbar, preferably 0.1 to 100 mbar is selected.
  • M n (OH prepolymer), the number average molecular weight of the OH-terminated prepolymer, is calculated here from the stoichiometry of the reaction of low molecular weight polyols HO-R 1 OH with polyisocyanates OCN-R 2 -NCO and is generally from 90.5 to 1000, preferably 91 to 800, more preferably 103 to 500 Da.
  • the number average molecular weight M n of the poly (urethane carbonate) polyol is preferably 350 to 5000, more preferably 400 to 4000, in particular 500 to 2500 Da.
  • the reaction can be catalyzed by bases or transition metal compounds.
  • bases or transition metal compounds examples include: magnesium hydroxide carbonate, dibutyltin oxide, bis (tributyltin oxide), titanium tetrabutylate, ytterbium acetylacetonate.
  • the poly (urethane carbonate) polyols according to the invention are liquid, waxy solid or else highly crystalline, depending on the nature and the proportions of their synthesis components and their molecular weight at room temperature.
  • a stoichiometrically analogous poly (urethane carbonate) polyol based on H 12 -MDI as the polyisocyanate component is completely amorphous and unable to crystallize.
  • poly (urethane carbonate) polyols according to the invention can be used in molecular weight-increasing polyaddition or polycondensation reactions, for example as starting materials for the preparation of polyurethanes, for example polyurethane cast elastomers.
  • this polyurethane carbonate polyol (OH number 74 mg KOH / g) were stirred at 75 ° C. in 398 g of 4,4'-diphenylmethane diisocyanate (Desmodur® 44M, Bayer MaterialScience AG) under nitrogen and reacted for 2 hours at 80 ° C.
  • the NCO content was determined to be 9.94% by weight of NCO (theory: 10.0% by weight) or 9.74% by weight after storage at 80 ° C. for 72 hours.
  • the viscosity immediately after the preparation was 1880 mPas (70 ° C), after 72 hours storage at 80 ° C 2190 mPas (70 ° C).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • General Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Polyesters Or Polycarbonates (AREA)
EP06003902A 2005-03-12 2006-02-27 Poly(uréthanecarbonate) polyols Withdrawn EP1700877A1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE102005011448A DE102005011448A1 (de) 2005-03-12 2005-03-12 Poly(urethancarbonat)polyole

Publications (1)

Publication Number Publication Date
EP1700877A1 true EP1700877A1 (fr) 2006-09-13

Family

ID=36095650

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06003902A Withdrawn EP1700877A1 (fr) 2005-03-12 2006-02-27 Poly(uréthanecarbonate) polyols

Country Status (9)

Country Link
US (1) US20060205912A1 (fr)
EP (1) EP1700877A1 (fr)
JP (1) JP2006249434A (fr)
KR (1) KR20060100201A (fr)
CN (1) CN1847278A (fr)
BR (1) BRPI0600766A (fr)
CA (1) CA2538652A1 (fr)
DE (1) DE102005011448A1 (fr)
MX (1) MXPA06002675A (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2886572A1 (fr) * 2013-12-17 2015-06-24 Bayer MaterialScience AG Utilisation d'alcools d'uréthane pour la fabrication de polyéthercarbonatepolyols
EP3098252A1 (fr) * 2015-05-26 2016-11-30 Covestro Deutschland AG Utilisation d'alcools, comprenant au moins deux groupes uréthane, destinés à la production de polyols de carbonate de polyéther

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX2014007223A (es) 2011-12-20 2014-09-22 Bayer Ip Gmbh Hidroxiaminopolimeros y procedimientos para su preparacion.
EP3498745A1 (fr) * 2017-12-18 2019-06-19 Covestro Deutschland AG Mousse rigide de polyuréthane ignifugée
CN111995728B (zh) * 2020-08-07 2022-04-19 山东一诺威聚氨酯股份有限公司 用于鞋材的非极性改性tpu及其制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3323684A1 (de) * 1982-07-02 1984-01-05 PPG Industries, Inc., 15222 Pittsburgh, Pa. Traegermaterialien mit duennen abriebfesten polyurethanbeschichtungen
US4820830A (en) * 1987-03-02 1989-04-11 King Industries, Inc. Certain hydroxyalkyl carbamates, polymers and uses thereof
US5621065A (en) * 1995-04-07 1997-04-15 Bayer Aktiengesellschift Polycarbonate diols, their preparation and use as starting products for polyurethane plastics

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1568248A1 (de) * 1966-02-11 1970-02-05 Huels Chemische Werke Ag Verfahren zur Herstellung von Carbonatgruppen enthaltenden Dihydroxyverbindungen
DE1770245C3 (de) * 1968-04-23 1979-11-15 Bayer Ag, 5090 Leverkusen Verfahren zur Herstellung von gegebenenfalls vernetzten Polyurethanen
DE1964998C3 (de) * 1969-12-24 1979-02-15 Bayer Ag, 5090 Leverkusen Verfahren zur Herstellung von Polyurethanelastomeren
USRE29224E (en) * 1972-05-04 1977-05-17 Bayer Aktiengesellschaft Polyurethane urea elastomers based on polycarbonate macrodiols
DE2221751C3 (de) * 1972-05-04 1978-08-10 Bayer Ag, 5090 Leverkusen Polyurethanharnstoff elastomere
US4105641A (en) * 1975-05-27 1978-08-08 Bayer Aktiengesellschaft Process for the preparation of aliphatic polycarbonates and polyurethanes therefrom
IT1227136B (it) * 1988-10-14 1991-03-19 Enichem Sintesi Policarbonati copoliesteri dioli, procedimento per la loro produzione e loro impiego.
DE19619237A1 (de) * 1996-05-13 1997-11-20 Bayer Ag Hydroxyfunktionelle Polyurethancarbonate, ein Verfahren zu deren Herstellung und deren Verwendung

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3323684A1 (de) * 1982-07-02 1984-01-05 PPG Industries, Inc., 15222 Pittsburgh, Pa. Traegermaterialien mit duennen abriebfesten polyurethanbeschichtungen
US4820830A (en) * 1987-03-02 1989-04-11 King Industries, Inc. Certain hydroxyalkyl carbamates, polymers and uses thereof
US5621065A (en) * 1995-04-07 1997-04-15 Bayer Aktiengesellschift Polycarbonate diols, their preparation and use as starting products for polyurethane plastics

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2886572A1 (fr) * 2013-12-17 2015-06-24 Bayer MaterialScience AG Utilisation d'alcools d'uréthane pour la fabrication de polyéthercarbonatepolyols
WO2015091246A1 (fr) * 2013-12-17 2015-06-25 Bayer Materialscience Ag Utilisation d'uréthane-alcools pour produire des polyols de polyéthercarbonates
US9957352B2 (en) 2013-12-17 2018-05-01 Covestro Deutschland Ag Use of urethane alcohols for preparing polyether carbonate polyols
EP3098252A1 (fr) * 2015-05-26 2016-11-30 Covestro Deutschland AG Utilisation d'alcools, comprenant au moins deux groupes uréthane, destinés à la production de polyols de carbonate de polyéther
WO2016188992A1 (fr) * 2015-05-26 2016-12-01 Covestro Deutschland Ag Utilisation d'alcools qui contiennent au moins deux groupes uréthane pour la préparation de polyéthercarbonatepolyols

Also Published As

Publication number Publication date
KR20060100201A (ko) 2006-09-20
DE102005011448A1 (de) 2006-09-21
MXPA06002675A (es) 2006-09-11
CA2538652A1 (fr) 2006-09-12
BRPI0600766A (pt) 2006-11-07
US20060205912A1 (en) 2006-09-14
JP2006249434A (ja) 2006-09-21
CN1847278A (zh) 2006-10-18

Similar Documents

Publication Publication Date Title
EP2014693B1 (fr) Elastomère de polyuréthane et de polyuréthane-urée à base de polyols de polycarbonate
JP3236214B2 (ja) ポリカーボネートジオール、その製造方法及びポリウレタンプラスチックの出発材料としての使用
EP0603675B1 (fr) Polyuréthanes aliphatiques et thermoplastiques sans catalyseur
DE68927281T2 (de) Polycarbonatdiolzusammensetzung und Polyurethankunststoff
KR100262246B1 (ko) 폴리우레탄 엘라스토머의 제조 방법
EP1632512B1 (fr) Acétylacétonates de métal comme catalyseurs de transestérification
EP3728385B1 (fr) Polyols de polycarbonate, prépolymères de polyisocyanate et polyuréthanes de polyuréthane-urée et élastomères de polyuréthane-urée à base desdits polyols de polycarbonate, prépolymères de polyisocyanate
EP1981923A1 (fr) Elastomeres moules de polyurethanne constitues de prepolymeres nco a base de 2,4'-mdi, leur procede de fabrication et leur utilisation
EP2155797B1 (fr) Prépolymères nco à faible teneur en diisocyanate monomère libre et leur production
EP1477508B1 (fr) Acetylacetonate d'ytterbium(III) comme catalyseur pour la préparation de polyols aliphatiques oligocarbonate
EP2448987B1 (fr) Procédé de préparation d'un polymère de polyuréthane comportant des polyesterpolyols portant des groupes terminaux hydroxyle secondaires
DE102007031546A1 (de) Verfahren zur Herstellung von thermoplastischen Polyurethanen auf Basis 1,5-Naphthalindiisocyanat
EP1671991A2 (fr) Prépolymères de polyuréthane réactifs ayant une faible teneur en diisocyanates monomèriques
EP1911782B1 (fr) Polyesterpolyoles, leur procédé de fabrication et leur utilisation
EP1700877A1 (fr) Poly(uréthanecarbonate) polyols
EP1024156B1 (fr) Elastomères coulés de polyuréthane à base de durol diisocyanate
EP3288993B1 (fr) Enveloppe en polyuréthane présentant une réception d'eau réduite et son utilisation
EP1765899B1 (fr) Procede pour produire des prepolymeres de polyurethannes aminofonctionnels
EP1997841A2 (fr) Procédé de fabrication de polyuréthanes thermoplastiques à base de 1,5-naphtalène diisocyanate
EP0442359B1 (fr) Polyuréthanes thermoplastiques
DE4311923A1 (de) Zweikomponentig zu verarbeitende Beschichtungszusammensetzung zur Herstellung von PUR-Elastomeren
DE102008012971A1 (de) Polyurethan-Prepolymer und hieraus hergestellte Polyurethan/Polyurea-Elastomere
JPH09286835A (ja) ２液注型用ポリウレタンエラストマー組成物、及び該組成物を用いたポリウレタンエラストマーの製造方法
DE2715566A1 (de) Polyurethanzusammensetzung

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI SK TR

AX Request for extension of the european patent

Extension state: AL BA HR MK YU

17P Request for examination filed

Effective date: 20070313

17Q First examination report despatched

Effective date: 20070417

AKX Designation fees paid

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI SK TR

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20080901